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<h1><a href="https://archiveofourown.org/works/27530296">Straight as a Bi</a> by <a class='authorlink' href='https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67'>CS_impala67</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Alternate Universe - Roommates/Housemates, Anal Fingering, Anal Sex, Angst with a Happy Ending, Awkward Sexual Situations, Barebacking, Best Friends, Bi-Curious Dean Winchester, Bisexual Dean Winchester, Blow Jobs, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Bottom Dean Winchester, Castiel/Dean Winchester First Time Having Sex, Coming Out, Dean Winchester Wears Panties, Dean Winchester is Not Heterosexual, Dean Winchester's First Time With a Man, Falling In Love, First Time Bottoming, Friends With Benefits, Friends to Lovers, Frottage, Gay Castiel (Supernatural), Gay Sex, Good Parent John Winchester, Hand Jobs, M/M, Mutual Masturbation, NSFW Art, Oral Sex, Panty Kink, Pining, Rimming, Sexual Experimentation, Switching, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester, Top Dean Winchester</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-11-12</td></tr>

<tr><td><b>Updated:</b></td><td>2020-11-22</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-08 06:34:35</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>11</td></tr>

<tr><td><b>Words:</b></td><td>13,435</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27530296</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Cas and Dean had been best friends since college. They had met when they were assigned to room together freshman year and had gotten along so well, they had decided to remain roommates all four years. Now, at almost thirty they even shared an apartment together. Castiel had been harboring a crush on his very straight roommate all of this time, knowing nothing would ever come of it. One night, while they were drunk at home, Dean lets slip that he had watched a gay porn video on accident and had jerked off to it and it got him curious to try more. Being drunk, Cas agrees to Dean’s suggestion that they experiment together since Cas is the only one Dean would feel comfortable trying it with. Can Cas help his friend discover truths about himself while guarding his own heart in the process?</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>94</td></tr>

<tr><td><b>Kudos:</b></td><td>296</td></tr>

</table>

<a name="section0001"><h2>1. Chapter 1</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>So excited to start writing a new fic!  I hope you enjoy!</p><p>Tags will be updated as the story progresses.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  
</p><p>Cas was just finishing typing up the last of the financial report he was currently working on, when he heard his roommate’s loud footsteps coming down the hallway from his bedroom. </p><p>“<span>Yo</span>, we’re drinking tonight.” Dean declared loudly. Cas could hear him shuffling around in the kitchen cabinets before he made his way into the living room and plopped himself on the couch beside Cas, two glasses and a bottle of whiskey in his hand.</p><p>“Why are we drinking?” Cas asked as he moved his laptop off his lap and onto the coffee table, before turning to rest against the arm of the couch, quirking his eyebrow at his friend as he awaited his reply. </p><p>“Do we need a reason?” Dean scoffed as he made himself comfortable. “I’m going crazy man! This stupid quarantine is driving me up the wall. I can’t stand being cooped up like this and I cannot stare at my computer screen another second. So, I’m drinking. And since I don’t feel like drinking alone, because <em>apparently </em>according to <em>Sam</em> that’s pathetic, you’re drinking with me.” Cas just rolled his eyes but acquiesced to Dean’s demand.</p><p>            Two hours later they were both way past tipsy and bordering on sloshed. Dean had the bright idea to play truth or dare. Cas put up a token protest, claiming they were not teens anymore and were way too old to be playing, but it didn’t take much arm twisting from Dean before he relented. He had to admit, he was having a good time too. There wasn’t a whole lot they didn’t know about each other, so they mostly picked dares, which lead to each of them drinking disgusting concoctions of the other ones making, prank phone calls, and one very funny rendition from Dean of Baby Shark, which had Cas wheezing with laughter. When he finally calmed down enough, he asked “Truth or Dare Dean?”</p><p>            “Oh man. Um…I think I’ll go with truth this time. Mix it up a bit.” His best friend relied, still chuckling from the last ridiculous dare. Cas had to think about this. What kind of question could he really ask? He decided to just go for a simple one.</p><p>            “Okay, what’s a secret of yours that I’d be surprised to find out?” He asked his friend, who started to blush. ‘Hm, interesting’. Cas though as he waited for Dean’s answer.</p><p>            “Okay, you um…If I tell you this, promise you won’t tell any of our friends?”</p><p>            “Of course.” Cas replied honestly. He’d never break Dean’s trust like that.</p><p>            “Okay so about a week ago, I uh…” Dean rubbed the back of his neck nervously, the blush having worked its way down his face. “I accidently watched a uh, a gay porn, and… I jerked off to it.” He finished with a whisper. Cas just stared at him dumbfounded.</p><p>            “How did you accidently watch a gay porn?” He asked the first question that popped into his head.</p><p>            “I dunno!” Dean shrieked all flustered. “I hit the wrong thumbnail or something, figured it was like a three-way maybe, but by the time I realized no girls were joining in, I’d already started, ya know.” He made a vague jerking off motion.</p><p>            “And you didn’t think to click over to a different video?” Cas asked curiously, making Dean’s face redden even further.</p><p>            “It was hot, okay! I kinda liked it.” He mumbled, and Cas almost didn’t hear it. Almost, but he had. He just stared at Dean, surprised at the admission. His roommate, his very <em>straight</em> roommate whom he had a crush on for years, had watched gay porn and <em>liked</em> it? He couldn’t wrap his mind around it. In fact, a few turns later it was still all he could think about. When Dean chose dare, he didn’t even think before he blurted out:</p><p>            “I dare you to watch a gay porn with me.” He wanted to take the words back as soon as they left his lips. But when he chanced a glance at Dean’s face, he held firm.</p><p>            “O-Okay.” Dean breathed out, sounding intrigued by the idea. “P-put one on your laptop then.” He said as he sunk back into the cushions. Cas quickly grabbed his laptop and fumbled with the keyboard to pull up his favorite site. He scrolled through the thumbnails to find one that looked good. One caught his eye of two guys sitting on a couch together, jerking off next to each other. Perfect. He clicked play and relaxed back into his side of the couch.</p><p>            The video played, and he watched the two guys on the screen. They were both watching something off camera, probably a porno, and Cas heated at the similarity of what he and Dean were doing. He felt himself begin to harden as he watched the men rub themselves over their jeans. He itched to reach down and rub his own cock, but he held back, not sure if that was currently allowed. That is, until Dean spoke.</p><p>            “Fuck…” Dean whispered and Cas glanced to the side and watched his best friend unzip his jeans, before plunging his hand inside.</p><p>Holy Shit. Guess they were masturbating together. Cas followed suit and undid his pants before reaching inside and grasping his hard cock. He breathed a sigh of relief once he touched himself and let out a low moan as he began to stroke it. He must have been louder than he thought if the “fuck Cas” Dean let out was any indication. He opened his eyes that he hadn’t even realized were closed, and met Dean’s awed stare. He was caught in those green eyes that he had come to love so much, unable to look away, even as they both stroked themselves inside their pants. His cock was so hard, there was barely enough room to stroke it inside his boxer briefs, but he was too scared to pull it out, not wanting to push too far for his straight roommate. He needn’t have been concerned because not long after, Dean made the decision for him, pulling out his own hard cock. Cas’ mouth began to water at the sight. Dean had a beautiful dick; hard and long, the tip flushed a bright red, with a dot of pre-cum beading on the slit.</p><p>“T-take yours out too.” Dean told him, breath deep with arousal, and Cas was quick to comply, pulling his own hard cock out of his pants. He gazed back up into Dean’s eyes as they both began to stroke in earnest. He couldn’t bare to look away, entranced by the lust filled look of the other man, and soon enough he was spilling over his own fist, with Dean following shortly after.</p><p>Once his brain came back online, and it hit him what they just did, it was like cold water being splashed in his face. He quickly excused himself, fumbling through an excuse to cut the night short, and he ran to his room, shutting himself safely inside.</p><p>“Fuck.” He groaned, puling desperately at his hair. What the hell had he just done?</p>
  </div></div>
<a name="section0002"><h2>2. Chapter 2</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>
  
</p><p>Dean woke up with a groan; his head felt like someone took a jackhammer to it, and his mouth tasted like ass. He pushed himself to a sitting position and held his throbbing head in his hands, trying to will away the massive hangover. He was about to stand up when the memories of the previous night rushed to the front of his brain. “fuck” he muttered to himself. Why did he decide drinking that much would be a good idea? And what possessed him to suggest truth or dare? He really should have listened to Cas when he said they were too old for it. Then he wouldn’t be sitting here, feeling like a coward too afraid to face his roommate. His roommate who he jerked off with last night. The same roommate who fled when they finished and left Dean sitting in the living room alone, regretting his entire existence.</p><p>            Fuck. He was such a fucking idiot sometimes. He’d obviously made Castiel uncomfortable with that stupid dare. No, wait. Cas was the one who suggested the dare, right? Ugh. His brain was currently a mess from all of the drinking last night. He needed coffee before he even attempted to try and figure out what he was going to do about last night.</p><p>            He slowly got up and made his way out to the kitchen where a pot of coffee was already sitting there brewed. Thank fuck that Cas usually woke up first. Dean fixed himself a cup before turning to make his way back to the safety of his room. Before he reached it, however, the bathroom door opened and Cas walked out, freezing when his eyes met Dean’s. They both stood there awkwardly, neither having a clue what to say apparently. Finally, Dean couldn’t stand the tension anymore.</p><p>            “So last night was, um… fun.” He blurted out the first thing he could think of as he rubbed the back of his neck nervously.</p><p>            “Um, yes…yes it was…fun” Cas mumbled in response, giving Dean a small smile in return. “Are we, um…good?” He asked shyly.</p><p>            “Yeah, ‘course we are Cas.” Dean affirmed with more confidence than he actually felt. He patted his friend’s shoulder and continued down the hall to his room, shutting the door behind him and placing his mug on his nightstand before he collapsed on the bed. He hadn’t been lying to Cas, last night had been fun. At least the parts he remembered clearly. He still couldn’t believe he actually admitted that he had watched a gay porn and liked it. He had planned on taking that secret to the grave, but apparently mixing alcohol and childish games had fucked that up. At least it was just Cas who knew. He knew he wouldn’t judge him, especially since he was gay and watched that type of porn.</p><p>He hadn’t been completely truthful though to his best friend. It had been no accident that made him click on that video. He had clicked it, knowing full well it was a gay video, considering he had purposely been browsing through the gay part of that site. Cas might know almost everything there was to know about Dean, but there was one thing he didn’t know. He couldn’t, considering Dean had only started really coming to terms with it himself, hence why he had been on that part of the site to begin with. Dean was pretty sure he wasn’t as straight as he always thought he was. In fact, he was almost positive he was bisexual. If he was being honest with himself, he had known this for about a decade, but he always just pushed those thoughts to the side, never really looking to close at them. Sure, he could appreciate a hot guy, but couldn’t everyone? Just because he could acknowledge when another man was good looking didn’t mean he was attracted to men, right? Yeah, he couldn’t even fool himself anymore. Especially not after a certain incident about a month ago.</p><p>He had been chilling on the couch one night, watching Dr. Sexy, when Cas had stepped out of the bathroom in just a towel. When Dean turned his head at the sound of the bathroom door, he froze at the sight of his half-naked best friend. He remembered being mesmerized by the droplets of water that dripped slowly down Cas’ toned chest, catching on the towel wrapped around his trim waist. The sharp hip bones peaking out above the towel had him chubbing up in his sweats and he had had to discretely cover his lap with a couch pillow. Ever since that night, he began having a realization. What he thought was just a normal appreciation was actually attraction. And he was pretty freaking positive he was attracted to his best friend.</p><p>That’s what had led him to finally clicking on that damn video. He wanted to see if any of it would turn him on. And oh boy did it! It hadn’t stopped at one either like he had told Cas. No. He had ended up watching at least five different videos that night and jerking off to the point that his dick became sore. What a revelation that night had been. He couldn’t remember ever coming that hard from any of the straight porn he had watched over the years. It had freaked him out a little too, realizing he wasn’t straight, but once he had a few days to think on it, he realized it wasn’t exactly a new development. He was just finally old enough that he didn’t feel like lying to himself anymore. He was almost thirty for crying out loud. If he wanted to have sex with a guy, so what? And the truth was, he really did. He wanted to have sex with a guy; and not just any guy, he wanted to have sex with Cas.</p><p>When Cas had dared him to watch a gay porn with him, he wanted to scream for joy. He had been shocked of course, but excited at the prospect of doing anything remotely sexual with him, baby steps and all that. Seeing Cas jerking himself off and coming had been the hottest thing he’d ever seen. He desperately wanted more to.</p><p>The next few days were spent slowly becoming normal around each other again, and by Friday, they were back to normal. Dean had also spent those days scheming up a way that he could get Cas to do more with him. He finally made a plan and as the two of them sat on the couch, drinking beer and eating pizza, he finally got the courage to broach the topic with Cas.</p><p>“Uh, hey Cas, can I talk to you about something?” He asked nervously.</p><p>“Of Course, Dean. You can always talk to me about anything.” Cas said sincerely as he turned to face Dean and give him his full attention.</p><p>“So, um…it’s about the other night, ya know, when we…” He made a vague jerking off motion with his hand as his face began to blush.</p><p>“You are referring to when we jerked off together” Cas stated bluntly, making Dean chuckle awkwardly.</p><p>“Yeah, um…yeah. So, the thing is…I’m uh, I’m pretty sure I’m not straight.” He stammered, but kept his head held high with the admission as he waited for Cas’ reaction. Cas’ eyebrows shot way up high into his hairline and his jaw dropped. It would have been comical if Dean wasn’t so nervous.</p><p>“Oh… Okay.” Cas stated, obviously not having expected that from Dean.</p><p>“Yeah. Um, so I was wondering, and you can absolutely say no.” He rushed to add. “But I was wondering if maybe, um, you could like, help me figure it out?” He asked unsurely. Cas was gaping like a fish at this point, eyes still wide in surprise before he cleared his throat.</p><p>“H-how do you w-want me to help you, um, figure it out?” Cas asked.</p><p>“I was thinking, since you are gay and all, maybe we can like, ya know, experiment together?” Dean replied hesitantly. When Cas just sat there staring at Dean in silence, he began to feel insecure. “You know what? Never mind, that was stupid. Forget I even said anything.” He rushed out embarrassed and began to stand up so he could rush to his room. Before he could take a step though, Cas’ hand reached out to grab his wrist.</p><p>“Yes!” Cas blurted. Dean looked up to meet Cas’ gaze and looked at him questioningly, unsure what he meant by that yes. Cas must have seen his confusion because he clarified. “Y-yes, I will experiment with you.” He whispered.</p><p>“Yeah?” Dean smiled shyly, excitement beginning to bloom in his chest.</p><p>“Yeah.” Cas smiled back.</p><p>“Ok cool.” Dean beamed. “So, uh, when do we start?”</p><p> </p><p> </p>
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<a name="section0003"><h2>3. Chapter 3</h2></a>
<div class="story"><div class="userstuff module">
    
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</p><p>            Cas was still slightly in shock. He was having trouble fully grasping that Dean might not be straight. That had been one of the absolute certainties he had always known; Dean was his best friend. Dean was his big crush. Dean was straight. It had always been easy to keep that crush to himself because he knew it would never go anywhere. How could it if Dean was straight? But now, everything had changed. That one certainty was no longer so. Dean hadn’t said he was bisexual or anything, which meant at this point he was probably just curious. He’d obviously been turned on by the porn, but that didn’t necessarily translate into being attracted to guys. It could have just been watching the act itself that he liked. But now he was sitting there, asking Cas to be his big gay experiment. Cas was torn. One the one hand, he’d have the perfect excuse to fool around with the guy he’d been crushing on for years. But on the other hand, would he be able to keep his feelings in check? Those thoughts were what made him delay in giving Dean an answer. But when Dean had tried to backtrack, Cas made the decision to go for it. When would he ever get this opportunity again? He just hoped it didn’t backfire on him.</p><p>            “Ok cool.” Dean beamed. “So, uh, when do we start?”</p><p>            “W-whenever you want.” He breathed out shakily. “What, um…what do you want to try?”</p><p>“Well…” Dean started, cheeks tinged pink as he twisted his hands together in his lap. “I kinda, um…I made a list.” He confessed before he reached into his pocket and handed Cas the folded sheet of paper he took out.</p><p>“Kissing, hand jobs, frottage…Ok I see you’ve done some thinking on this.” Cas said as he read the list Dean had made. He began to blush at some of the words, ‘anal’ in particular. “So, you, um…it seems you want to try a bit of everything.”</p><p>“Y-yeah, I mean…why not?” Dean shrugged before clearing his throat. “If you’re okay with that. I uh, wasn’t sure what you prefer, like what…um…position.” He whispered, clearly uncomfortable talking about it.</p><p>“Position. You mean if I top or bottom?” Cas asked, a smirk tugging at his lips. It was kind of cute to see Dean squirm about sex. He normally loved to brag about getting laid, so this was a treat to see.</p><p>“Y-yeah. That.” Dean chuckled awkwardly.</p><p>“Well I’m a switch so I like both. Although I tend to top more than I bottom.” Cas admitted with his own shrug. He couldn’t deny that it was a little weird to be talking so openly with Dean about this.</p><p>“Oh, um…okay, so maybe we could try it both ways? I mean, not yet ya know, I’m not ready for that yet. Kinda wanna work my way up to that.” Dean chuckled again.</p><p>“Of course, whatever you want Dean. But I do have one condition.” Cas told him.</p><p>“What’s that?” Dean asked curiously.</p><p>“No kissing.” He said firmly.</p><p>“Oh…. okay, um why not?” Dean sounded disappointed, but maybe Cas was just hearing things.</p><p>“I only kiss in a relationship. Kissing is very intimate for me.” He explained, which was mostly true. He had definitely kissed on first dates and on some one-night stands. But kissing Dean would be too intimate. It would be bad enough having sex with him and trying to protect his heart. There was no way he could kiss his friend and not let his feelings show. That was one thing he planned to stand completely firm on.</p><p>“Okay, got it. No kissing.” Dean nodded in understanding. “I was thinking, maybe we could um…watch another porn but this time, like jerk each other off?” He said in question and Cas felt his pulse begin to race at the thought.</p><p>“Okay, y-yeah we could try that. Now?”</p><p>“Sure. Pull up a video on your laptop.” Dean instructed.</p><p>Cas complied and opened his laptop that was sitting on the table in front of him, and navigated to his favorite site. He scrolled down the page till a video caught his eye; it was a video entitled ‘gay friend jerks off straight friend’ and Cas chuckled to himself as he clicked play and sank back into the cushions. He felt Dean shift on the couch and settle beside him, thighs toughing.</p><p>The video played in front of them, and he felt Dean’s breath hitch before he placed his hand on Cas’ leg, slowly working it up until he cupped Cas’ bulge. Cas gasped in surprise and shifted his hips up to push against Dean’s hand. He quickly reached down to unbutton his jeans and push them down below his hard cock, and he looked over at Dean’s lap watching him do the same. They both reached out simultaneously to grasp the other’s dick in their hand and let out twin groans of pleasure.</p><p>“Fuck…” Dean whispered and Cas turned his head just enough to make eye contact. He saw lust and arousal clear in his friend’s gaze and he slowly stroked his hand up and down the hard length in his fist, making Dean’s eyes roll “Fuck that feels so good Cas…” He felt Dean tentatively stroke his cock and he sighed in pleasure, eyes closing as he sank into the feeling.</p><p>“Yeah…. yeah it does.” He agreed. They stroked each other, strokes getting faster the closer they came to orgasm, and before he knew it, he felt Dean come all over his fist moaning Cas’ name as he did. Cas followed quickly after.</p><p>“Fuck, Cas…” Dean breathed out in what sounded like awe and Cas opened his eyes to look at his best friend. Dean seemed to be leaning closer, and Cas turned his head just in time as Dean ended up kissing the side of his face. “Fuck! Sorry Cas I forgot the no kissing thing.” Dean apologized and Cas felt his heart clench. He desperately wanted to feel Dean’s lips on his, but he knew he made the right decision.</p><p>“It’s fine. Just remember going forward.”</p><p>“I will. I uh…that, that was fucking hot Cas.” Dean said breathily, voice deep and husky.</p><p>“Yeah.” Cas agreed, as he attempted to catch his breath. Hot was an understatement. He didn’t know how he was going to make it through anymore of this without wanting more than Dean was offering though. He knew it was just sexual for his friend. Dean would never want him the way Cas hoped he would.</p>
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<a name="section0004"><h2>4. Chapter 4</h2></a>
<div class="story"><div class="userstuff module">
    
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</p><p>“What? No way!” Cas exclaimed in disbelief at his friend. There was no way he heard him right.</p><p>It was Saturday night and after a whole day of doing absolutely nothing, Dean somehow convinced him to drink with him again. Not that he really had to twist Cas’ arm too hard, seeing as he was also bored out of his mind. This pandemic had them both going stir-crazy at this point. At least during the week, they both had to work from home most of the day. Castiel worked as a tax accountant so it had been easy for him to work remotely since his work was all on computers anyway. Dean was an insurance claims rep, so his work was also fairly easy to do remotely, although he was on the phone all day with customers, unlike Cas who corresponded mostly through email. But at least they remained busy with work and both had a solid income coming in. They were some of the lucky ones.</p><p>But the weekends? That was a different story. They were used to going out with friends, or at least out to the bar, just the two of them. Now that they were pushing thirty, they didn’t party as much, but it was still nice to have the option to go out on a Friday or Saturday night. Instead, they were stuck inside because of a mandatory quarantine in their area. It was sad when Cas actually looked forward to grocery shopping, because it meant he had a valid reason to leave his house.</p><p>So, boredom, <em>again</em>, led them here; both of them were tipsy and Dean just confessed to another secret that Cas couldn’t believe.</p><p>“I’m dead serious man! Rhonda Hurley, back in college, remember her?”</p><p>“Vaguely” Cas replied, still in shock.</p><p>“We were fooling around and she dared me to try on her panties. And I kinda liked ‘em. So, before I left the next morning to do the walk of shame, I stole ‘em.” Dean finished with a shrug as he took another sip from the bottle of whiskey he was drinking.</p><p>“Y-you um… Do you still have them?” Cas asked, voice slightly wavering as his body started reacting to the thought of his best friend in the panties.</p><p>“Yup” Dean affirmed as he nodded his head before smirking “Why? Ya wanna see em?”</p><p>Cas gulped before nodding in reply “Y-yes.”</p><p>Dean just chuckled before he stood up and made his way to the bedroom, leaving Cas sitting on the couch waiting. Cas took a few deep breaths to try to get his heart rate under control. He had to be dreaming. He even pinched himself to check, but nope, this was real life; this was actually happening. After a few minutes, he heard the bedroom door and turned his head to look, and his jaw dropped at the sight he was met with. There stood Dean in a pair of satin pink panties. As he walked closer, Cas’s breath hitched at the mouthwatering sight of his straight best friend in such feminine clothing. They sat low on his trim hips and hugged his package perfectly. As Dean turned around, Cas could see how they framed his sexy ass perfectly too.</p><p>“So…. what do ya think?” Dean asked with a smirk once he was in front of Cas, though years of being his friend meant Cas could hear the uncertainty in his question.</p><p>“Come here.” Cas growled as he reached for his friend’s hand to tug him closer, making him fall to straddle Cas’ lap. Dean’s hands went to Cas’ shoulders to steady himself and Cas grabbed the other man’s hips, caressing them. “Fuck Dean, you look stunning.”</p><p>“Y-yeah? You like ‘em?” Dean asked hesitantly, voice low with clear arousal. Cas pulled the other man’s hips down, grinding his hard cock up against him.</p><p>“Don’t ask stupid questions.” He growled as he rocked their bodies together.</p><p>“Fuck, Cas…” Dean moaned, and Cas could feel his friend’s cock harden against his own, which was digging painfully into his zipper. He reached down to undo his pants and pull his hard cock out, lining it up with Dean’s panty clad length. When he grinded them together again, they both let out twin moans.</p><p>“Fuck, that feels good.” Cas said as his cock slid against the soft material encasing his best friend’s cock.</p><p>“Y-yeah. God Cas!” Dean groaned as he rocked his hip down onto Cas’ lap. Cas leaned forward to capture Dean’s pebbled nipple between his teeth and gently bit down, making the other man whimper “Yes! Fuck!”</p><p>Dean sinfully gyrated his hips as Cas continued the assault on his nipple and he heard the other man call out his name, before he felt the hot dampness seep through the panties from Dean’s come. That’s what pushed Cas over the edge and soon he was coming too, messing up the front of the dainty fabric.</p><p>“I think we ruined these.” Cas managed through heavy breathing; voice raspy after that spectacular orgasm. Dean chuckled in response</p><p>“Guess you’ll have to buy me a new pair.” He teased, and Cas smiled as he looked up at him. He didn’t know how long they stared into each other’s eyes, but he felt something pass between them, something big, and his heart clenched in response. Dean leaned forward again, and Cas knew what was about to happen and he almost let it, but at the last second, he turned his head once more, receiving a kiss on his cheek, that he knew Dean meant for his lips. “Shit. I forgot again. I swear I’ll try to remember next time Cas.” Dean apologized.</p><p>“It’s fine.” Cas told him. But it wasn’t, not really. He desperately wanted that kiss and part of him wished he had let it happen. But he knew he had to draw the line there. Because, once he kissed Dean, there was no way he’d ever be able to stop, and that’s not what this was about. This was just helping his friend come to terms with his sexuality, nothing more. He needed to remember that.</p>
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<a name="section0005"><h2>5. Chapter 5</h2></a>
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</p><p>So far, everything they had done together had been amazing and Dean had loved every minute of it. It was official; he was definitely bisexual. He had no doubts about that fact now. But he wasn’t ready to tell Cas that yet. Not because he was worried about judgment, of course; that would be silly. No. He wasn’t ready to tell Cas yet because he didn’t want this new thing between them to end. The whole experimenting together thing was supposed to be so that Dean could figure out for sure if he was bi, and if he admitted he was, then he would have no excuse to do anything sexual with Cas. He’d have no reason to see him naked, or touch his hot as fuck body anymore. He wasn’t ready for that.</p><p>Dean wasn’t stupid either; he knew why he wasn’t ready for it to end. He had feelings for his best friend that went way past lust and into that other L-word that he wasn’t ready to say quite yet. But it was obvious that Cas didn’t feel the same way. Cas had known he was gay the entirety of their friendship, and never once had he even hinted to having any feelings towards Dean. Cas didn’t even want to kiss him because that would be too <em>intimate</em>, and if that wasn’t a clear enough sign that Cas didn’t feel the same way as him, well, Dean didn’t know what else could be. It royally sucked but whatever; nothing he could do about it except milk whatever he could from their current arraignment. With that in mind, he made his way to the living room where Cas was sitting on the couch, scrolling through his phone. Dean plopped his ass on the seat next to his friend.</p><p>“Blowjobs.” He blurted out simply, in his usual classless way. He watched as his roommate choked on air before turning to Dean with his classic bitch-face on; the one he used when he was annoyed at Dean for something.</p><p>“Really Dean?” He said, unamused.</p><p>“What?” He quipped with a shrug. “It’s what’s next on my list.”</p><p>“You’re ridiculous.” Cas rolled his eyes.</p><p>“So is that a yes or….”</p><p>“Sure. Why not?” Cas shrugged as he leaned back into the back of the couch and spread his legs. “Get to it.” He said, eye brow quirked.</p><p>“Seriously? Just like that?” Dean hesitated.</p><p>“You’re the one who suggested it Dean. And if this is about you ‘experimenting with your sexuality’” Goddamn Dean loved when Cas used air quotes. “Then obviously you should be the one doing the blowing. So… go on, blow me.” Cas finished with a smirk, almost like he was daring Dean, or calling his bluff. But Dean wasn’t bluffing; he really wanted to try this. So, he got down on the floor and shuffled over to kneel in front of Cas. He looked into those baby blues he was so fond of and he reached for the waistband of Cas’ pants and slowly pulled them down to release his cock, which was beginning to harden up. He stroked it a few times in his fist to get it the rest of the way there.</p><p>“I’m probably gonna be so bad at this.” He warned before he licked a tentative stripe up the underside of the hard length.</p><p>“Y-you’ll do fine. Juts watch the teeth.” Cas assured him.</p><p>Dean began licking small stripes up the side of his cock, till he reached the head. He could hear little hums from the other man that sounded appreciative and it gave him the confidence to continue. He bravely took the head of the cock into his mouth, and he tasted the precum that had beaded on the tip. It was a little bitter, but not too bad, so he sucked gently to get another taste.</p><p>“Fuck…” Cas whimpered as he reached his hand to run it through Dean’s hair in encouragement. Dean lowered his head, taking Cas’ hard cock further into his mouth. He went a little too far and gagged a bit, so he pulled back and wrapped his hand around what he couldn’t reach with his mouth.</p><p> “Y-you don’t need to…. fuck…to deep throat Dean. Just…. uh…just suck on, on what you can.” Cas told him in between breaths. Hearing the clear arousal in Cas’ voice had Dean craving more. He began bobbing his head up and down, sucking on the head each time he came up. He fondled Cas balls with his free hand as he continued his ministrations. After a little while, his jaw began to ache, but he was determined to do this. He doubled his efforts, bobbing his head faster as he stroked his hand in time with his mouth. He was so hard in his pants that he released Cas’ balls and reached town inside his boxers to stroke his own cock. It was difficult maintaining the rhythm of his head while he jerked himself, but if the noises Cas was making were any indication, he was doing fine.</p><p>“F-fuck Dean. I’m gonna come!” Cas called out as he tried to pull Dean off his cock, but Dean wouldn’t let him. He wanted to taste it. He was never as thankful as he was right now that he and Cas had already had the whole safe sex talk after this first started and they both were clean. He sucked harder on the head as he stroked his own dick and Cas gripped his hair tight. Dean felt the cock in his mouth swell up, and then he tasted the salty come that shot out, into his mouth. The first taste had him spilling over his fist, and he moaned, swallowing every last drop that landed on his tongue. He felt Cas shudder, so he pulled back and reached up with the back of his free hand to wipe the corner of his mouth. His knees were shaky so he turned to collapse on his ass against the couch.</p><p>“So…How did I do?” His tone was joking but he really hoped he did good. He heard Cas chuckle above him and he looked up to meet his eye.</p><p>“That…that was amazing Dean. You sure that was your first-time sucking cock?” Cas teased, making Dean chuckle with him.</p><p>“Promise. I know I got cock-sucking lips man, but yours was definitely the first I ever sucked. Fuck that was hot. My jaw is killing me.” He said as he wiggled his jaw side-to-side, rubbing it with the hand not covered in come.</p><p>“You get used to it.” Cas replied, and Dean hoped he did. He hoped he had plenty of chances with Cas to get used to it. One could only hope.</p>
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<a name="section0006"><h2>6. Chapter 6</h2></a>
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</p><p>After the blowjob, Dean couldn’t get enough. It was like Cas was his drug and he was addicted to the other man; to his taste, to his smell, to his touch. Every time they were together, Dean wanted to ravish him and he was getting so damn frustrated at the no kissing rule. He desperately wanted to know if those lips felt as soft as they looked. If the man kissed even half as good as he sucked cock, then Dean wanted some of that. After Dean had blown him the other night, Cas had returned the favor once their dicks weren’t too sensitive anymore, and holy hell had it been fantastic. No one had ever sucked his cock that good. Cas sure as hell knew what he was doing and made Dean feel like he had died and gone to heaven. All he could think about was, if his mouth felt that good, his ass must feel even better and Dean wanted to sink into that tight heat as soon as possible. With that in mind, he grabbed a couple of condoms and the lube from his nightstand drawer and pocketed them before making his way to Cas’ room. He knocked and when he heard Cas yell to come in, he entered and shut the door behind him.</p><p>            “Hello Dean. What’s up?” Cas asked as he moved his laptop off of his lap and onto the desk beside his bed.</p><p>            “So, I was thinking…” Dean began nervously as he wrung his hands together. “We’ve uh, we’ve done the hand jobs and blow jobs. And uh…the whole frottage thing already…”</p><p>            “Yes. We’ve been making our way through your list.” Cas stated, head titled in confusion before he seemed to understand where this was going.  “Ah, are you here to try another item?” He asked.</p><p>            “Y-yeah. Yeah, I was um, I was thinking maybe we could try anal?” Dean asked hesitantly. He could feel his ears turn red just saying that word. Cas’ eyebrows shot up in surprise.</p><p>            “You want me to fuck you?” He asked in surprise.</p><p>            “No! No, no I meant, um… I meant I wanna fuck you.” He rushed to clarify, face heating in both embarrassment and arousal. The thought of being fucked intrigued him, but he wasn’t quite ready for that yet.</p><p>            “Oh, okay.” Cas nodded in understanding. “You uh, you wanna do that now?”</p><p>            “Yeah, I mean, only if you’re game.”</p><p>            “Sure, yeah, just um… just give me a couple of minutes to go um, freshen up.” Cas said as he stood up.</p><p>            “Dude you don’t gotta freshen up for me. Didn’t you just shower earlier?” Dean asked confused. Cas chuckled fondly at him before smirking.</p><p>            “I was trying to be discreet Dean. I need to go clean myself out if you are about to stick your dick up my ass.” Dean immediately felt stupid that he hadn’t caught on before.</p><p>            “Oh, um, right. Yeah I didn’t think of that.” He shrugged. His face had to be the color of a tomato at this point.</p><p>            “Yes. It’s not like fucking a vagina. It can get messy. Which is why anal usually isn’t done spur of the moment. I’ll be quick though. Just make yourself comfortable until I get back.” Cas winked at him, before he left the room.</p><p>Dean took his shirt off and decided he might as well take his pants off too before he climbed in Cas’ bed to sit against the headboard. He waited anxiously for Cas to come back, the anticipation of what they were about to do was making his cock chub up in his briefs. He was about to have full on sex with his best friend. His best friend who he was slowly falling in love with. Fuck, this was either a really good, or a really bad idea, he wasn’t sure which.</p><p>After what felt like forever, but was probably only a few minutes, Cas walked back in the room with just a towel wrapped around his waist and Dean felt his mouth water at the sight. Those damn hips should be illegal. He must have been obvious in his ogling because Cas called him out on it.</p><p>“Like what you see?” He teased Dean as he slowly made his way over to the bed.</p><p>“Y-yeah, Fuck Cas. You’re hot.” He managed to choke out inelegantly.</p><p>“You’re not so bad yourself Dean.” Cas dropped the towel before kneeling on the bed and shuffling close to Dean.</p><p>“I, um, I brought condoms and lube in my pants pocket on the floor.” He told the other man who bent down to retrieve said items before turning to face the room, giving Dean a close up view of the ass he would be sinking into shortly.</p><p>“I’m gonna prep myself so just sit back and watch.” Cas instructed as he leaned forward on all fours putting his ass even closer to Dean’s face. Dean gulped at the view. Cas flicked open the cap and poured some lube on his fingers. He rubbed them together to warm it up before reaching behind himself and rubbing a circle around his rim before he began to sink his digit inside his tight hole.</p><p>“Fuck.” Dean whispered. He reached out to rub his hand up Cas’ thigh. “God that’s sexy.” Cas just hummed in response before he began fingering himself, quickly adding a second finger and scissoring them to stretch his hole. Dean just watched, mesmerized at the sight in front of him. Cas soon deemed himself ready and removed both fingers before turning and straddling Dean’s legs. He handed him the condom which Dean hurriedly put on after he pulled his briefs off. Cas grabbed Dean’s cock to line it up with his hole, and before he knew it, Cas was sinking down on his hard cock, both of them groaning once he bottomed out.</p><p>“Fuck your cock feels so good in me.” Cas said through heavy breaths. Dean grabbed his hips, rubbing his thumbs over them.</p><p>“God, fuck Cas y-you’re so, uh…so tight.” He chocked out. They both took a minute to get used to the feeling before Cas began lifting up and sinking back down, making Dean moan at the tightness gripping his dick.</p><p>“Fuck…yes….” Cas moaned as he gyrated his hips, swiveling them in figure eights before riding up and down again, blowing Dean’s mind. The pleasure was so intense and he couldn’t hold back anymore. He braced his feet on the mattress and started fucking up into his friend.</p><p>“Fuck yes! Right there!” Cas screamed and Dean continued his assault, fucking up into that spot over and over as Cas continued screaming profanities. “Fuck I’m gonna…. I’m gonna cum!”</p><p>Dean felt Cas clench hard around him, and then he watched the come shoot out of Cas’ cock, untouched, to land all over Dean’s chest. He bucked up a couple more times, before he too was thrown over the edge, coming hard inside the condom in Cas’ ass.</p><p>Once they caught their breaths, Cas rose up off of Dean’s cock, both of them wincing at the feeling, before they cleaned themselves up with tissues beside the bed. Dean laid down on his back, pulling Cas down with him to lay on his chest as he held him tight.</p><p>“Never pictured you for a cuddler.” Cas teased as he swirled his finger lazily over Dean’s chest.</p><p>“What can I say? I’m a cuddle slut.” Dean shrugged with the shoulder Cas wasn’t laying on. “Fuck that was good.”</p><p>“Mhmm.” Cas hummed in agreement as they lay there together. Dean heard Cas’ breathing even out and realized the other man had fallen asleep when he heard a small snore. Fuck he wished he could keep this forever. Just the two of them laying together like this was exactly where he wanted to be. His last thought before sleep took him too was that he was definitely irrevocably in love with Castiel Novak.</p>
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<a name="section0007"><h2>7. Chapter 7</h2></a>
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</p><p>Castiel woke up slowly, his dream fading to the background as he became aware of his surroundings. The bright light shining through the curtains made him groan and try to roll over away from it. That’s when he realized a few things. One, he wasn’t alone in his bed. That became clear when he couldn’t move because a strong arm was wrapped around his waist, holding him in place. And two, there was something poking him in his backside. The moan he heard behind him clued him into exactly what that thing was.</p><p>            “Mmm Cas.” Dean moaned behind him as he ground his hard cock against Cas’ ass. Between the grinding and the rough sound of sleepy arousal coming from the man at his back, Cas felt his own cock hardening up between his legs. They were both still naked, having fallen asleep after sex the night before and when Dean’s cock slipped between Cas’ cheeks, he let out his own moan.</p><p>            “Dean…. Fuck…” He pushed back against the other man. He still felt wet and open from the previous night. “Fuck me.”</p><p>            “I need another condom.” Dean told him.</p><p>            “Fuck the condom. We’re both clean. I wanna feel you.” He begged.</p><p>            “Fuck…” Dean cursed as he lined up his cock and pushed into Cas’ hole making Cas hiss at the stretch. He probably could have used a bit of prep but he was too impatient. He loved lazy morning sex.</p><p>            “You okay?” Dean asked in concern, halting his movements.</p><p>            “Yeah, yeah…just…fuck…. just sore. Keep going.” He assured him. But instead of pushing in, he felt Dean pull out. Before he could ask why, Dean pulled on his hip making him roll over onto his back. Dean climbed between his legs and positioned his cock back at Cas’ entrance.</p><p>            “I wanna see your face.” He explained and then he was pushing in again. Cas wrapped his arms around Dean’s back as the other man bottomed out. “Fuck you’re so fucking tight Cas.” He said through gritted teeth.</p><p>            “Your cock feels so big…” Cas groaned. He wrapped his legs around Deans lower back, digging his heels into the top of Dean’s ass. “Move, please.” He begged. Luckily Dean was quick to comply and began slowly thrusting inside Cas’ tight channel. “Fuck yes, like that…god, Dean!” He babbled, moaning as Dean fucked into him.</p><p>            Their bodies slid together, grinding against one another as Dean moved inside him. Cas’ hands glided up and down Dean’s back, touching any skin he could get ahold of. Dean didn’t speed up, he just lazily thrust into him. It felt so much more intense than last night. This felt heavy; like they were making love. He knew that’s not what Dean intended, since he didn’t feel that way about Cas, but he couldn’t help wishing. Couldn’t help feeling like this meant more than just sex. Like they were two boyfriends making love after cuddling all night. His heart clenched at the thought and he had to hold back the tears he felt trying to well up. He didn’t want to ruin this.</p><p>            “Fuck Cas…” Dean moaned as he shifted his body, the new angle making him hit Cas’ prostate dead-on.</p><p>            “Right there!” Cas called out, and Dean sped up hitting it over and over again. He reached up and grabbed Dean’s short locks in his fist, their eyes locked together and then Cas was coming, harder than he ever had before. In a moment of weakness, he pulled Dean’s head down and crashed their lips together in a heated kiss. He felt Dean moan into his mouth and then Dean’s thrust faltered as he coated Cas’ insides with his release. The kiss lasted minutes, or maybe seconds, he couldn’t tell; But when he realized what he did, it felt like a bucket of ice-cold water was thrown on his face. He began to panic, pushing Dean off of him as he scrambled to get up.</p><p>            “Cas, Cas! What’s wrong?” Dean pleaded, most likely confused at Cas’ sudden change of mood.</p><p>            “I’m sorry, I… I can’t do this anymore. We need to s-stop this.” Cas stuttered.</p><p>            “What happened Cas? Did I do something wrong.” Dean moved to come closer but Cas backed up and held his hands out.</p><p>            “Please just leave.” He choked out; his throat tight with emotion. He felt the panic clawing its way through his body.</p><p>            “<em>Please</em> Cas. Please tell me what I did wrong.” Dean begged but Cas just shook his head.</p><p>            “Its me. I just need s-some space. P-please.” He felt a tear drop down his cheek and he turned so Dean wouldn’t see.</p><p>He heard the other man sigh, but he did as Cas asked. He heard Dean pulling on his clothes and then leaving the room and Cas finally crumpled, succumbing to the sobs that he had been holding back. He fell onto his bed, shaking and crying. He was so stupid. He had fucked up and crossed the line he had been so adamant about drawing. He knew kissing Dean would be a mistake, but he had been so caught up in the moment that he couldn’t help himself. And now all he felt was crushing heartbreak. He was so stupid to even start all of this with Dean. He had known that going into this, but he had wanted to take whatever he could get from his friend; whatever little bit of intimacy, even if it had only been sex. That was more than he had ever hoped he’d even get from his best friend.</p><p>He had probably just fucked up their friendship beyond repair now though. All because he hadn’t been able to separate his feelings from sex with Dean. God he was so stupid and pathetic. And of course, he had to go and do all of this during a damn pandemic where neither of them could leave the house. It was going to be absolute torture to see Dean every day now and not touch him anymore; not to mention how awkward it was going to be now that they had had sex and Cas had freaked out so bad. But he was being truthful, this had to stop. He couldn’t continue this whole experimenting thing with Dean. It already hurt too bad, and it would only get worse if they kept going. He just had to hope that they would be able to go back to the way things were before this all had started. He really couldn’t bare the thought of losing Dean as a friend.</p><p>He eventually cried himself back to sleep, praying he hadn’t fucked things up irrevocably.</p><p>           </p>
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<a name="section0008"><h2>8. Chapter 8</h2></a>
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</p><p>When Dean got back to his own room, he sat on his bed with his head in his hands. He had no idea what the fuck just happened. They had been having sex-<em>hell-</em>more than that; it had felt like he was making love to Cas, which was something he had never done before. When he looked into Cas’ eyes, it almost looked as if Cas felt the same. And then Cas had gone and kissed him, making Dean feel like he had died and gone to heaven. He couldn’t remember ever being kissed like that before in his life. He’d felt a tiny glimmer of hope that maybe, <em>just maybe</em>, Cas felt the same. But then Cas had gone and pushed him away, saying he was done and needed space. Maybe he had realized Dean was catching feelings and felt like they needed to stop because he didn’t feel that way.</p><p>Dean was still so confused. He didn’t know what to do. He regretted ever starting this thing in the first place. He had been so selfish, asking Cas to be his experiment. Now he had probably fucked up their decade long friendship in a matter of weeks. All because he had been thinking with his dick instead of his head.</p><p>“Fuck!” He yelled to his empty room and he tugged at his hair in frustration. He needed to talk to someone. He needed to get this out. He wracked his brain trying to figure out who he should call. Finally, he decided he should call his brother. They had always had each other’s backs and Dean knew Sam wouldn’t care that he had a thing for guys. Hell, Sam had gone to California for college, and was now working as a Lawyer specializing in discrimination lawsuits. If anyone wasn’t going to judge him, it would be Sam. So, Dean grabbed his phone off the nightstand and dialed his number. After three rings, he finally picked up.</p><p>“Hey Dean.”</p><p>“Heya Sammy.” He sighed, as he flopped back onto his pillow.</p><p>“What’s wrong?” Sam asked, concern clear in his voice. He was always able to tell when something was up with Dean.</p><p>“Sammy, I uh, I fucked up.”</p><p>“What happened?”</p><p>“I think I ruined my friendship with Cas.” He mumbled, rubbing his hand down his face.</p><p>“Dean. I’m sure it can’t be that bad. You two have been friends for a decade now.”</p><p>“Yeah, I know. But uh…fuck…I… I should probably start with the fact that I’m bi…” He waited with baited breath for his brother’s response to that admission. He felt both relief and dread from coming out to someone for the first time.</p><p>“Oh…” He heard his brother’s surprise through the phone line. The longer he waited for more of a response, the more he began to panic that maybe he had been wrong. Maybe his brother wasn’t okay with the fact that he also liked guys. Before he could send himself into an anxiety attack though, Sam spoke again.</p><p>“Sorry, you just surprised me. I had no idea Dean. But uh…thanks, you know, for telling me. I know how hard it can be to come out.” Dean felt his body untense as relief washed over him.</p><p>“So, uh…you cool with it? With me liking guys?” He asked, still a little uncertain.</p><p>“Yeah of course Dean. You’re still my big brother. Your sexuality doesn’t change that.” Sam was quick to assure him.</p><p>“Ok cool. Thanks. That um, that means a lot.” He felt his eyes being to mist over but he quickly wiped the tears away before clearing his throat. “So um, the next part of this is a little TMI.” He warned.</p><p>“Like that’s ever stopped you.” Sam quipped making Dean chuckle.</p><p>“True. So, anyway…” He relayed everything that had happened between him and Cas since that first drunken night, up until now, including the part where he was hopelessly in love with Cas. Sam was quiet as he let him talk before, he finally responded.</p><p>“Well, first of all you are an idiot.”</p><p>“Hey!” Dean retorted, but Sam carried on.</p><p>“No, you really are Dean. It’s never a good idea to have sex with a friend. Especially not a best friend. “</p><p>“I know. I know okay?” He sighed. “I didn’t anticipate catching feelings though.” He mumbled.</p><p>“Yeah, but that’s exactly why its never a good idea.”</p><p>“Yeah I’m an idiot.” Dean agreed. “So, what should I do now?”</p><p>“You really need to talk to Cas. Give him a couple of days, since he asked for some space. But then you should really tell him how you feel Dean.” Sam urged.</p><p>“Do I have to.” He whined petulantly, like a five-year-old.</p><p>“If you want to move past this, yes you should. Otherwise its going to eat away at you and that never ends well.”</p><p>“Okay, maybe you’re right. Thanks Sammy.”</p><p>“No problem. I’ll talk to you later jerk.”</p><p>“Alright, bye Bitch.” He hung up the phone. Maybe Sam was right; maybe he should just tell Cas how he felt.</p><p>He spent the next few days thinking on it, before he made his decision. Things had been awkward between him and Cas after that morning, and he couldn’t take it anymore. He decided enough was enough and so he made his way to Cas room, but before he could knock, he heard Cas voice inside. It sounded like he was talking to someone on the phone. He knew he shouldn’t ease drop but he was always too nosy for his own good and so he listened quietly.</p><p>“Fuck, Charlie…. I don’t know what to do…yeah, I know…. yes, I was stupid…. yes, I know…. but what if he never wants to speak to me again…. but what- yes, I know we’ve been friends for a long time, but…fuck. But what if I tell him and he hates me? I don’t know…. What am I gonna do? Just say “oh hey Dean, oh by the way I’m in love with you?” …”</p><p>Dean gasped and before he could think about what he was doing, he pushed open the door. “Cas?” He asked in awe. Cas jumped and turned to face him, eyes wide and jaw slack.</p><p>“Charlie I gotta go.” He said quickly as he hung up the phone. “How long were you listening outside my door?” He asked with a quivering voice.</p><p>“Long enough. Did you mean it Cas? Are you really in love with me?” He asked with baited breath, hope filling his heart as he waited for Cas’ response.</p><p>With trembling lips Cas breathed out a quiet “Yes.”</p>
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<a name="section0009"><h2>9. Chapter 9</h2></a>
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</p><p>“How long were you listening outside my door?” Cas asked Dean. His voice was quivering in fear and embarrassment. He prayed Didn’t hear his conversation with Charlie.</p><p>“Long enough. Did you mean it Cas? Are you really in love with me?” Fuck. Dean wasn’t supposed to find out; not like this. He hadn’t even been sure he wanted to tell Dean, but unfortunately the cat was out of the bag.</p><p>With trembling lips Cas breathed out a quiet “Yes.” He stared at the bedroom floor, tears welling in his eyes. This was it; the moment Dean would tell him their friendship was over. He hadn’t even in a million years expected what came next. Dean rushed to him and crashed their lips together, pulling him into a passionately heated kiss. Cas froze in shock, before his lips got with the program and he kissed back, titling his head to deepen their kiss. It lasted till they both had to come up for air, and Dean pulled back before resting his forehead against Cas’.</p><p>“Fuck Cas. I love you too.” Dean whispered and Cas could hardly believe his ears. He pulled back to look Dean in the eye.</p><p>“What? What do you mean?” He asked, breaths still heavy from the kiss.</p><p>“I’m in love with you Cas.” Dean breathed out in the space between them.</p><p>“H-how? I thought you were just experimenting?” Cas asked, still confused. How could Dean be in love with him? Hadn’t he just been questioning his sexuality?</p><p>“Heh, yeah…about that…” Dean chuckled nervously, rubbing the back of his neck. “Can we sit down?”</p><p>“Sure. Yeah.” Cas nodded before moving to sit on his bed, leaving enough room for Dean, who sat down facing him. He grabbed Cas’ hand in his and rubbed his wrist with his thumb.</p><p>“I haven’t been completely, um…completely truthful Cas.” Dean began. “I’ve been pretty sure I’m not straight for longer than I let on. Truth is, I only really asked to experiment with you because I wanted you. You’re hot, ya know?” He shrugged. “But after the first time we touched, I started catching feelings, beyond just wanting to have sex with you. And then the more we did, the harder I fell. I’ve been positive I was Bi since almost the beginning, but I, heh…. I didn’t want to admit that, because I didn’t want to stop all of this.” He waved his hand between the two of them. “So yeah, I uh I love you, I’m in love with you Cas.” He smiled then, and Cas just stared at him as he processed everything Dean just said.</p><p>“You’re an idiot.” He blurted out, making Dean groan.</p><p>“Fuck, why do people keep saying that?” Dean whined, as he threw his head back.</p><p>“Who else told you that?”</p><p>“Sammy did. I called him that morning after you kicked me out of your room cuz I had to tell someone. He told me I was an idiot for even starting this thing with you.” Dean sighed.</p><p>“Wait. You told Sam about us?” Cas asked in surprise. “He knows your bi?”</p><p>“Yeah. Came out to him and everything. He took it well. You know he’s a bleeding-heart hippie. Even got the long hair for it.” Dean joked.</p><p>“Wow. Well good for you Dean.” Cas smiled. “So, um…where does that leave us now?” He asked shyly.</p><p>“Depends. You mad at me for lying?” Dean asked hesitantly, and Cas just rolled his eyes.</p><p>“No Dean. Its not like I was completely truthful either.” He admitted.</p><p>“Whaddya mean?”</p><p>“Well when we started this, I already had feelings for you. Dean, I’ve been in love with you for years.” He confessed, slightly embarrassed to finally admit to that. But it was also freeing to be able to tell Dean after so many years of pining.</p><p>“No shit? Wow Cas, I had no idea.” Dean exclaimed.</p><p>“I didn’t exactly want you to know.” He shrugged. “I thought you were straight this whole time, and that I’d never have a chance with you. So, when you said you might not be straight and that you wanted to experiment with me, I figured it would be my only chance to be with you like that. But it’s why I refused to kiss you. I knew once I did, it would hurt too bad not to really be with you.”</p><p>“Oh, so that’s why you pushed me away the other day! Because you kissed me.” Dean snapped his fingers in realization.</p><p>“Exactly. I knew I couldn’t keep doing this with you after that. It would hurt too bad.”</p><p>“Fuck. We’re both idiots.” Dean chuckled, causing Cas to chuckle and nod in agreement.</p><p>“I guess so.”</p><p>“So then, do you wanna give this thing with us a shot? Like for real?” Dean asked sounding hopeful.</p><p>“I’m in if you are.” Cas smiled.</p><p>“Awesome.” Dean smiled back. They both stared at each other, dopy smiles on their faces before they both started giggling like teenagers.</p><p>“Oh, I should probably call Charlie back. Now that we’ve resolved this.”</p><p>“Good idea.” Dean agreed. “Hey, why don’t you FaceTime her and we can tell her the good news together.” He suggested.</p><p>Cas scooted next to Dean and hit call as he held the phone up so they both could see. Charlie answered on the first ring.</p><p>“Hey Cas, Hey Dean!”</p><p>“Hello Charlie.” Cas smiled at his friend.</p><p>“So…. don’t leave a girl hanging!” They both laughed at her and Dean put his arm around Cas shoulder and placed a kiss to his forehead, making Charlie squeal in delight.</p><p>“Yes! I knew it! I’m so happy for you guys!” She yelled excitedly. They talked for a few minutes before ending the call. Dean turned to look at Cas and reached his hand up to cradle his jaw.</p><p>“So…can I kiss you now?” He smirked.</p><p>“I think that would be appropriate.” Cas quirked his eyebrow playfully. And then they both leaned in, lips touching gently before they tilted their heads to deepen it. It wasn’t heated, or passionate, but it was perfect. Cas sighed into it and ran his fingers through Dean’s hair. It only lasted seconds before they pulled back to smile shyly at each other.</p><p>“I think I wanna try bottoming next.” Dean stated out of nowhere and Cas just shook his head.</p><p>“You are ridiculous Dean.”</p><p>“I think I’m adorable.” Dean smirked “Come on! It’s next on my list!” He argued and Cas just rolled his eyes.</p><p>“We’re still doing that list of yours?” He quirked his eyebrow in question and Dean just shrugged.</p><p>“Why not? There’s still stuff I wanna try.”</p><p>“Alright. But if you really want to bottom Dean, we should work up to it. How do you feel about rimming?”</p>
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<a name="section0010"><h2>10. Chapter 10</h2></a>
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</p><p>“Oh fuck.” Dean moaned at the first lick of Cas’ tongue. He had been hesitant when Cas first asked about it. The idea of someone licking his asshole didn’t sound pleasant, or sanitary for that matter. But apparently it felt <em>really</em> good, or so Cas said. So, after taking a <em>very</em> thorough shower, here he was, naked, face down and ass up in Cas’ bed while Cas kneeled behind him. His boyfriend (<em>holy shit</em> he had a <em>boyfriend</em> now!) had a cheek in each hand, spreading them apart to expose his hole. He felt self-conscious and vulnerable; his ass had never been touched or even looked at like this by anyone before. But as Cas started to rim him, it was hard to really care. “God that feels good.” He moaned.</p><p>“I told you.” Cas gloated before he dove back in with fervor, licking broad stripes from Dean’s balls, up his perineum and across his virgin hole. God it felt so fucking good. How had he never experienced this before? Fuck he could do this every day. Cas placed his lips around his hole and sucked, before pointing his tongue and pressing in.</p><p>“Fuck.” He whimpered, so lost in pleasure he couldn’t even think straight. His boyfriend’s tongue kept pushing in, fucking his hole, and Dean felt his body shaking from how good it was. “God Cas, just like that.” He babbled.</p><p>Cas continued eating him out, like Dean was his last meal. Suddenly, he felt Cas’ finger rub against his hole, beside his tongue, and Dean wanted it. “Do it Cas. Finger me.” He begged, wanting to know how it felt to finally feel something deep inside him.</p><p>“Are you sure Dean?” He asked as he continued rubbing the tight ring of muscle.</p><p>“Y-yeah, fuck…I want it Cas. Put it in me.” He pleaded as he pushed his ass back, trying to get it inside him. He felt Cas lean over into the nightstand, before he straightened back up behind Dean. He could hear a cap flip open and then a wet finger rub against his rim. He held his breath as Cas pressed on his hole, and then it was pressing inside, having breached the tight muscle. It burned a little as Cas sunk in, but he licked around his finger, soothing the bit of pain. Dean felt Cas wiggling his finger around, and then there was a jolt of intense pleasure as he hit something inside him.</p><p>“Fuck!” He yelled. “Was that my fucking prostate?” He wondered aloud, and he heard Cas chuckle behind him.</p><p>“Yes Dean.”</p><p>“Fuck, n-no wonder why, huh, why guys like to…to bottom” He stammered through heavy breaths. Cas just hummed in reply before he pushed against it again, making Dean keen in pleasure. Soon Cas was thrusting his finger in and out, making Dean moan loudly, and screaming out each time that magical spot was hit. His orgasm was so close. He reached down to grab his cock, and it only took half a dozen strokes before he was coming all over the pillow below him. He felt the finger leave his ass and then he collapsed onto the bed, body shaking too much to hold himself up anymore. He heard a noise behind him so he turned his head to look and saw Cas stroking his own cock.</p><p>“Fuck yeah Cas. Come on me.” He goaded his boyfriend. Cas groaned and then spilled his release all over Dean’s ass before collapsing on the bed too, half laying on Deans back.</p><p>“Fuck Dean.” Cas heaved, gravely voice sending shivers down Dean’s spine.</p><p>“We are so doing that again.” He exclaimed, making Cas laugh.</p><p> </p><p>**********************</p><p> </p><p>Dean’s leg was shaking as he sat on the couch, waiting for the video call to go through. He felt his boyfriend place a comforting hand on his knee.</p><p>“Relax, Dean. Everything will be fine.” Cas tried to reassure him. But Dean couldn’t help it, he was nervous as hell.</p><p>“What if they don’t take it well?” He asked for the fifth time in the last ten minutes.</p><p>“Dean, your parents love you. I’m sure they won’t care sweetheart.” He felt warmth flow through him at the term of endearment. It helped calm him a bit, right as his parent’s faces popped up on the screen.</p><p>“Hey baby.” His mom smiled at him through the screen.</p><p>“Hey mom. Hey dad.” He waved at them.</p><p>“Hello Mary. Hello John.” Cas said beside him.</p><p>“Hello Castiel.” They both greeted.</p><p>            “How are my two boys?” His mom asked. “I feel like I haven’t seen you guys in forever!”</p><p>            “Yeah I know Mom. This damn quarantine sucks.” He agreed. “We’re good though. I got Cas here for company. That’s uh…” He rubbed his neck nervously. “That’s actually something I wanted to talk to you about. Something I gotta tell you.” Fuck he was so nervous. At twenty-nine years old, he was finally about to come out to his parents. He felt like he was at the edge of a cliff, about to jump off, and he just hoped they’d be there to catch him.</p><p>            “What is it baby? What do you need to tell us?” His mom asked, clearly concerned.</p><p>“Um, I uh…I’m…” He started shaking, but Cas grabbed his hand and he began to relax. He could do this. “I’m bisexual. And um…Cas is my boyfriend now. We uh, we just started dating.” There. It was out there now. He watched the screen for his parent’s reaction, and all he could see was confusion on their faces. He had kind of expected that though. Not every day your grown son comes out.</p><p>“What do you mean Dean? You just started dating?” His mom asked, eyes scrunched in confusion.</p><p>“Exactly what I said Ma. I’m bisexual, and me and Cas just started dating last week. He’s my boyfriend now.” He wasn’t sure which part was confusing her.</p><p>“But I thought you guys had been dating since college?” She asked.</p><p>“What?!” He squawked indignantly, as Cas lost it beside him, throwing his head back and laughing. “ What do you mean you thought we were dating?!” He yelled. This whole conversation was getting away from him.</p><p>“Isn’t that why you guys moved in together?” His dad asked.</p><p>“No! Geez…” He rubbed a hand over his face in frustration. “So, this whole time, for <em>years</em>, you thought the two of us were a couple?”</p><p>“Well, yeah. I mean, you two have been inseparable since college. You moved in together. You guys even switch off holidays between us and Cas’ family.” His mom explained.</p><p>“And you never once mentioned that to me?” Dean couldn’t believe this. He had been so worried about coming out to his parent’s and it turned out, not only did they already know he liked dudes, but they thought he had been dating one this whole time. “I never even came out to you!”</p><p>“We figured you knew that we knew. You’d always crushed on male celebrities; I didn’t know it was a secret.” His mom just shrugged and Dean couldn’t help but laugh at the ridiculousness of the situation.</p><p>            “Alright, well this has been fun and all, but we’re gonna go now. I’ll talk to you guys later.” They said goodbye and he ended the call. He turned to look at Cas who was still laughing beside him, wiping the tears out of his eyes. “Yeah, yeah, laugh it up Chuckles.” He scoffed.</p><p>            “H-holy shit Dean! That was…the funniest thing…I’ve ever, ever heard.” He chocked out between laughs. “I can’t believe…th-they thought we’ve been dating…this…this whole time.”</p><p>            “God, what even is my life right now.” He muttered, sending Cas into another fit of giggles at his expense. It was a good thing he loved the freaking dork.</p><p> </p>
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<a name="section0011"><h2>11. Chapter 11</h2></a>
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</p><p>He had been dating Cas for a month now, and things were amazing. He’d moved into Cas’ room and got to wake up next to the love of his life every morning. To say Dean was happy was an understatement. He had big plans for tonight too. It was officially their one-month anniversary and he wanted it to be special. Call him a sap or whatever, he was finally in a relationship with someone he loved and he wanted to celebrate that.</p><p>            It wasn’t freaking easy planning an anniversary during a pandemic either. It’s not like he could go out and get anything, or send Cas away to set anything up, so he had to be sneaky about the whole thing. He’d spent the last week ordering a few things online, and hiding the packages in the closet of his old room as they came. Cas had been suspicious but then Dean distracted him with a blow job and all was forgotten. That was definitely a perk of them dating now. It was easy to distract Cas with sexual favors, or persuade him. And Cas didn’t seem to be complaining either.</p><p>            Dean had cooked them a nice dinner, even lighting candles to try and fancy it up. Cas had just smiled that adorable gummy smile of his and told Dean he loved him before they began eating. As he finished chewing the last bite of his meal, he pushed his plate away.</p><p>            “Ok, so I have a little surprise for you.” He said to Cas.</p><p>            “But I didn’t get you anything Dean.” His boyfriend pouted, adorably.</p><p>            “Don’t worry, this is something for both of us to enjoy.” He assured him. “But you gotta give me like ten minutes to set it up. I’ll text you when you can come in the bedroom.”</p><p>            “Oh, is it a sexy surprise?” Cas wagged his eyebrows and Dean chuckled fondly at him.</p><p>            “Something like that.” He winked as he got up and made him way into the bedroom, shutting the door behind him.</p><p>He had already taken a shower before dinner, making sure to clean himself out. He’d even used a freaking enema he had ordered online. That had been incredibly awkward. He quickly got undressed and grabbed the giant bow from the box where he hid it under the bed. He laid himself down on the bed on his stomach, reaching behind him to place the ridiculous bow on top of his ass. His present was that he was planning on finally bottoming for Cas tonight. It’s something he had been wanting, but had been too nervous to bring up again after the first time he’d mentioned it. Cas hadn’t mentioned it either, probably not wanting to pressure Dean. But he remembered Cas saying he preferred to top, so he really wanted to give this to him. What better present than giving up his anal virginity. Fuck, he was nervous though.</p><p>He took a few deep breaths before texting Cas that he was ready. He waited with baited breath, until he heard the bedroom door open and Cas let out a gasp. He turned his head and saw his boyfriend’s slack jaw.</p><p>“Happy Anniversary.” He smirked to cover his nerves.</p><p>“Holy shit Dean. Is this what I think it is?” Cas asked as he slowly made his way to the bed.</p><p>“I uh…I want you to make love to me Cas.” He whispered.</p><p>“Fuck, Dean. You look so beautiful right now. Even with the ridiculous bow.” Cas’ voice was deep and gravely, and his eyes were dark with lust. Dean wiggled his ass, making the bow shake from side to side.</p><p>“Well, my virgin ass is your present. I figured I’d wrap it for you” He joked.</p><p>“And what a present it is.” Cas growled before he reached out to stroke the firm globes of his ass. He threw the bow to the side before climbing up on the bed straddle Dean’s thighs. He leaned down to cover Dean’s naked body with his own before whispering in his ear. “I can’t wait to be inside you.”</p><p>“Fuck Cas. Please.” Dean begged. Cas quickly stripped off his own clothes and reached into the nightstand for their bottle of lube. He moved to sit in between Dean’s legs, spreading them apart to make room. A cold, wet finger circled his hole before it pushed in, sinking all the way to the last knuckle. Cas had already fingered him a few times, so Dean was used to this part; although this time, it wasn’t the main attraction. No, that would be finally taking Cas’ cock inside him. Just the thought had his cock so hard beneath him. Cas wasted no time stretching him out, and before he knew it, the fingers left his ass and were replaced by the blunt head of Cas’ cock at his hole.</p><p>“Are you ready Dean?” Cas asked once he lined himself up.</p><p>“Y-yeah Cas. I wanna feel you inside me.” He pleaded and then he felt it; the head of Cas’ cock pushed in, breaching the tight ring. His eyes clenched tight as he tried to relax around the large girth stretching him open.</p><p>“Fuck.” He whimpered as he reached for Cas’ hand, grasping it in his own to help ground him. There was a sharp pinch of pain as Cas slowly pushed more of his cock in, and Dean took deep breaths, willing his muscles to relax. It hurt, <em>fuck</em> it hurt, but Cas went slow, only pushing in a little at a time to let Dean adjust to the intense feeling of being stretched open around a cock for the first time.</p><p>“You’re doing so good sweetheart. You’re taking my cock so well.” Cas praised as he rubbed soothing circles with his free hand on Dean’s lower back, holding his other hand tight in comfort. Dean felt him bottom out, hips touching Dean’s ass. “I’m all the way in now Dean. You took my whole cock.”</p><p>“Fu-uck Cas.” He whimpered. He felt so full, so stretched open. It still hurt, but not as bad. He felt his muscles begin to relax against the intrusion and he took a few shaky breaths before he told Cas to move. His boyfriend began gently circling his hips, barely pulling out before grinding back in deep and after a few minutes, the pain began to fade.</p><p>“More Cas.” He begged and Cas complied. He slowly pulled out, until the head tugged on his rim, before he pushed back in just as slow. “Fuck.” He moaned as the pain started turning to pleasure. Cas continued his slow thrusts, leaning over to cover Dean’s body with his own. The change in angle had Cas nailing his prostate making Dean yell in pleasure. “God, Fuck, Yes Cas!”</p><p>“Your ass feels so fucking good Dean.” Cas growled in his ear, sending shivers of lust down Dean’s spine. He turned his head enough to capture Cas’ lips in his as the other man fucked into him harder.</p><p>“Fuck yes! Your c-cock feels s-so good Cas.” He groaned into Cas’ mouth in between kisses.</p><p>Over and over, Cas thrust into him, nailing his prostate on every few thrusts and Dean felt his orgasm building. “I’m gonna come!” He yelled, before he felt his body tense up and his cock erupt below him, completely untouched. He heard Cas groan behind him and his hips falter before he felt his insides being painted in his boyfriend’s release. It could have been hours later, but was probably only minutes when Cas finally pulled his softening cock out of him and flopped on his back next to Dean, pulling him to lay on his chest.</p><p>“Best. Present. Ever.” Cas rasped through heavy breaths and Dean chuckled into his chest.</p><p>“I’m glad you liked it Sunshine.” He smiled, lazily playing with the smattering of hair on his boyfriend’s chest. Cas kissed the side of his head.</p><p>“How do you feel?” Cas asked, a touch of concern in his voice. Dean wiggled his hips a little and winced.</p><p>“A little sore. But good Cas. That was…fuck, that was good.” And it really was. Even though there had been some pain, the pleasure had far outweighed it and he knew the more they did it, the easier it would be each time. “I definitely want to do that again once my ass has a break.”</p><p>Cas chuckled before tilting Dean’s chin up and placing a chaste kiss on his lips.</p><p>“I love you so much Dean.” He smiled.</p><p>“I love you so much too Sunshine. You make me happy.” Dean smiled back,</p><p>“When skies are gray?” Cas asked with a smirk, and Dean just shook his head.</p><p>“God you are such a dork.” He said fondly.</p><p>“I know. Its one of the reasons you love me though.” Cas batted his eyelashes.</p><p>“It definitely is.” Dean agreed before resting his head back on Cas’ chest. They’d have to get up and shower soon, but for now? For now, he was content to just lie here, relaxed in the arms of the man he fell head over heel with for as long as they could. This was where he belonged.</p>
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